


bounce back

by SebGray



Category: Critical Role (Web Series)
Genre: Alternate Universe - Human, Alternate Universe - Modern Setting, Alternate Universe - Modern: No Powers, Dildos, Dom/sub, Drunk Sex, Explicit Consent, Explicit Sexual Content, F/M, Masturbation, Nonbinary Character, Post-Break Up, Strap-Ons, Trans Character, Trans Male Character, Vaginal Fingering, Vibrators
Language: English
Status: In-Progress
Published: 2020-01-01
Updated: 2019-12-31
Packaged: 2021-02-27 14:55:04
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 8,020
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22058896
Author URL: https://archiveofourown.org/users/SebGray/pseuds/SebGray
Summary: After suffering bad breakups and discovering their odd connection, Caleb and Jester decide to have a one-night-stand that lasts...a little bit longer than one night.
Relationships: Jester Lavorre/Caleb Widogast
Comments: 4
Kudos: 54





	bounce back

**Author's Note:**

> This chapter contains explicit sexual content.

Caleb sat at the bar, bones feeling heavy, too busy staring into space to even properly drink. He had been there for a while, with the only interruptions being when he paused his sorrow to drain his glass and the times he occasionally asked for a refill. The bartender, though, was the type of guy who wouldn’t talk to patrons when they were in a rough patch. This was definitely one of those times. Right now, Caleb was tired and just wanted to get plastered until someone cut him off and then get a taxi home. Well...could you call the place you’re crashing at a  _ home _ , really? He sighed and took another long drink.

The door opened and closed. Caleb didn’t bother to look, really. But he saw a flash of blue hair and caught a strong scent of vanilla and cinnamon as the new person sat next to him. “One piña colada, please,” she said. Her voice high and sweet and strongly accented. Eastern European, Caleb guessed, but he hadn’t been to enough of the area or listened to enough of the accents to properly tell them apart by country. As soon as the bartender's back was turned to make the drink, her head slowly slid to the counter and stayed there as she groaned. It lasted about sixteen seconds and Caleb was pretty sure everyone in the bar could hear it.

He awkwardly smiled and asked, “Rough day?” before taking another sip of his whiskey.

“More like a rough month,” she replied, leaning back in her stool. “I’m so tired of pretending to be happy, you know? Like, I haven’t been able to tell anyone about the fact that the guy I thought was going to fucking propose dumped me for some stupid German girl because I’m not ‘serious enough’. Like, seriously, ‘ _ serious enough _ ’? What kind of a comment is that? Just because I’m not a Ph-fucking-D and I draw and vlog for a living doesn’t mean I’m not wife potential, you know?”

Caleb froze, not really expecting a rant, but then nodded and said, “Ja, I get it. I got dumped, too.”

“See? You get me.” The girl took her drink from the bartender and started sucking it down so fast Caleb was surprised she wasn’t getting brain freeze.

“Ja, I suppose,” Caleb said. But then he stopped and looked at Jester oddly. “Wait. You said he ended up with a German girl?”

The girl nodded. “Yeah. Why, do you think you know her?”

“Was her name Astrid by any chance?” Caleb asked trepidatiously.

“Let me check. I managed to get screenshots of his Instagram because he still hasn’t blocked me yet.” She looked it up on her phone. “Her Instagram username is @astridpfeff.” She mispronounced the last bit, sounding out the “p”, but no, that was Astrid. “Is that her?”

Caleb nodded gravely, sighing. He had expected that she was with someone else, but he hadn’t thought it was someone who had also dumped somebody. “Ja, that is her. That is my ex.”

The girl’s eyes went wide as her jaw dropped. “No way! What a small world! You’d think in a city like New York, we wouldn’t run into each other like this.”

“Indeed.” Caleb sighed and sipped more whiskey. The bartender went about getting him another glass.

“Well,” said the girl after taking a long sip on her piña colada, “when did you guys break up?”

“Earlier today,” said Caleb. “She packed up my stuff while I was at work. Told me she wanted me gone. We got into an argument about it. She said she wanted someone who could pay off her student loans, and held mine over my head.” He frowned. “We had been together since high school. Ten years. I was planning on proposing when my book got published but...she didn’t give me the chance.”

“Wow. I’m sorry.” The girl offered a comforting smile, almost moving her hand towards him, but stopping. “But...do you want to know the truth?”

Caleb furrowed his brows. “What do you mean by that?”

“Do you want to know what might be the real reason she broke up with you?”

He sighed, looking away. Did he? After a moment, he said, “Alright. Tell me. I might as well kill whatever good feelings I have left for her.”

The girl took a deep breath and said, “She was cheating on you. With my ex.” Caleb looked at her but said nothing. She continued. “Rob was already cheating on me with her before we even broke up. And then he took me out to dinner at our favorite cafe and I thought he was going to propose and he said he was breaking up with me. Cause of the whole ‘not serious’ thing. And then, like a dick, he expected he would be able to stay for a few weeks while everything was settled, like...hell fucking no? You dumped me and my name’s on the fucking lease, not yours! So he started moving out. But before he left, of course, he just  _ had  _ to take a shower. Couldn’t wait until he got to wherever he wanted to go. And he was an idiot, like always, and left his phone in the living room. So I looked through it. And I found this contact name, ‘Sunflower’. So I looked at it. Sure enough, dating back a fucking year, he’s been flirting with this girl, sexting her, taking her out on dates. He sent her his dick. Which, I can tell you as his ex, not nearly that impressive, especially in practice.” She stopped mid-rant, probably having realized the fact that Caleb had basically pressed up his face against the counter. “Oh. Yeah. Sorry.”

“It is fine, I just...I thought it was just about finances.” He sighed.

“I’m sorry.” The girl patted his back. Her hand felt heavy. Being touched by a stranger suddenly made Caleb realized how terribly the affection in his relationship had dwindled even before the breakup, and exactly how touch-starved he was. “If it makes you feel any better, Rob really isn’t as hot as you,” she added. “Whoever this Astrid is, she’s definitely downgrading.”

Caleb felt his cheeks warm beyond the effects of the alcohol, and he sat up, smiling just a little more, letting her hand drift off his back. “Thank you. To be honest, I am kind of glad you told me. It...would explain a lot. Looking back, I can see all the problems. She said she had a lot of long shifts at work, she bragged a ton about all the overtime she was getting, but her contribution to the bills never increased, and she always talked about being broke. I thought maybe she was paying off her loans. Now that I know that, looking back, she was probably out with him. Plus she just...sort of stopped talking to me even when we were together. No ‘I love you’, no affection, not even any pleasantries. She was just always on her phone. Probably texting him.” He sighed. “Ah, well.”

“Hindsight is twenty-twenty,” said the girl with a shrug. “But yeah, that happened to me, too. Out all the time, constantly making excuses, never being affectionate. Our sex life used to be crazy good but then it turned it just me jerking off every so often when he wasn’t home and then having to hide it because he thought watching porn was as bad as cheating.”

Caleb raised an eyebrow. “Seriously? The guy who  _ actually  _ cheated on you thought that you watching porn was as bad as cheating?”

“Yeah, he became really accusatory a lot. If I ever went to see my friends, he’d accuse me of hooking up with them. If I ever went out to do some drawing in a cafe, he said I was just doing it to flirt with the barista. If I texted someone, I was sexting them, and I had to show him everything.” She scoffed. “He was such a jerk. I’m surprised I didn’t dump his ass first.”

“Ja.” Caleb nodded. “I am sorry.”

“No, no, it’s fine. It wasn’t your fault. We both got hurt.” She sighed. “At least my relationship only lasted two years, and not  _ ten _ . That makes me feel really sad for you, to be dating someone for that long and for them to betray you like that. You don’t deserve it.”

“I mean...how would you know? I don’t have much to offer.” He sighed and stared into his whiskey, not yet drinking it. “I’m a writer who lives off of a minimum wage job. I barely made ends meet even with Astrid and her manager's position. I’ve got student loans up to my ears and a useless creative writing degree and no real experience outside of just writing and being a fucking barista, so all I can get is a fucking barista job. No wonder Astrid cheated on me.”

“Hey!” the girl said sharply. “Don’t say that about yourself! None of those things are bad, much less bad enough for someone to cheat on you. You don’t deserve that sort of shit. You deserve nice things. Like love and self esteem and someone to suck you off.” Caleb looked up at her with even more of a blush and her pretty tan skin had turned a bright red around the cheeks as she returned to her drink, probably trying to shut herself up.

“Well... thank you for that.” Caleb took a long drink of his whiskey and sighed. The silence came and lingered, like a creepy acquaintance who’d wrap their arms around you when you hardly knew them. Then Caleb perked up a little and asked, “Well, have you talked to your friends about it?”

She groaned. “They’re all out of town. We all met in college and then went our separate ways. Plus they’re all so busy all of the time, and they have so many of their own problems. Like, I love them, but they’re not the best at helping me out when I need it. Plus, like...I don’t like talking over text anyways. I want to talk to people face to face, you know? And…” She sighed. “I didn’t want to seem weak. They see me as this cool person who has her shit together and helps everyone out and cheers them all up, but like...I can’t be that and be sad that I just got cheated on and dumped, you know?”

“I can understand that, ja. Do you have any family?”

“Well, I have my mom, but she lives in California, and she’s always busy with work or therapy or whatever so whenever I want to talk to her she has to leave or she doesn’t have the time so...I don’t really have anyone to talk to.”

Caleb smiled a little, nudging her with his shoulder. “You have me now.”

She grinned. “Thank you. That means a lot.” They just shared eye contact for a good few seconds, the silence less awkward and sad and a bit more comfortable now. Then the girl said, “Since we’re going to be friends now, I might as well introduce myself. I’m Jester, and my pronouns are she/her and they/them.”

“Ah, you are nonbinary?” Caleb seemed a bit intrigued. He didn’t have any other friends who weren’t cis.

“Yeah! What about you?”

“Oh, uh, Caleb. He/him only. I’m trans. I haven’t met a lot of people who were either.”

“Well, you have me!” Jester grinned. It was, for the first time, full and happy and...wow, she was gorgeous. Maybe it was the alcohol, maybe it was the weird intimacy they had now, or maybe it was the sudden freedom of being single for the first time in a decade, but Caleb felt a little bolder.

“You have a gorgeous smile,” Caleb said to Jester with admiration.

Jester giggled and oh, shit, their laugh was somehow better than their smile. “I know, right? Thank you! You have a really beautiful smile, too!”

Caleb didn’t even realize he was smiling at that moment. His blush returned with vigor. “Thank you. You are very sweet.”

“Thanks!” Jester smiled as her gaze took him in fully. She bit her lip and Caleb’s heart thudded. “You’re really hot,” they said, their voice a bit lower and...not threatening, really, but definitely the type of voice that made him feel like he wanted to submit to them, but a really good way. He hadn’t felt this way in a long time.

“Are you...busy tonight?” Caleb asked. He couldn’t believe he was asking her this.

“No. You?” They raised an eyebrow.

“Nein. I’m off work tomorrow.” He smiled. “Shall we?”

She smiled. “I think we should.” Jester took out her wallet and turned to the bartender. “Let me cover his tab, too.”

Caleb started to protest, hand going to his wallet.

“Let me treat you! You were dumped today! You deserve it.” She shoved a debit card in the bartender’s hand.

“Fine. But I cover the tip.” Caleb pulled out a twenty and handed it to the bartender as well.

“That’s fine. I don’t have much cash anyways.” They signed the little receipt and handed it back to the bartender, then put their card away and shoved their wallet in their purse. Caleb laughed a little. He didn’t notice it was shaped like a cupcake.

They got up and headed out. “My apartment is right down the street,” she said.

“Good, because I’m currently staying with a friend of mine. I can’t afford an apartment on my own.”

“Oh, I’m sorry.” Jester took Caleb’s hand. Her skin was cool and soft against Caleb’s warm, rough hands. They walked together, holding hands like a normal couple. It was a bit weird for Caleb, but it felt...right. Better than the past few years of dating Astrid.

They came up to her apartment building. It wasn’t half bad. Better than where Caleb was now. She opened the door with a key, then led Caleb upstairs to her apartment, unlocking it and letting Caleb in. She closed the door, set down her keys and purse, and then suddenly, her hands and mouth were all over Caleb. She pinned him to the wall, kissing him intently. His breath was stolen from his lungs, replaced with a suddenly high, dizzy feeling that he just adored. Gods, her lips were soft and she had this strong, commanding energy Caleb hadn’t felt in fucking forever, and if he wasn’t horny before, he sure as hell was now. “Jester,” he moaned softly. 

“Caleb,” Jester said. Eventually, she slowed things down a little, saying, “Sorry, I just had to kiss you. I’ve been wanting to do that for the past five minutes.”

“Oh, no, it is fine,” said Caleb. It was more than fine. It was fucking  _ divine _ .

“Before we go any further, do you have any limits? Any hard no’s?”

After a moment’s thought, Caleb said, “Please do not belittle me. Like, teasing is fine, and a little name-calling here and there is all good, but I do not like being mocked or made fun of. Also, you know, nothing extreme. No bodily fluids, breathplay, stuff like that.”

“Okay. I don’t like being made fun of either, so there’s that. Also pinning me down is a no go. Do you have any preferred safe words?”

“I never really used them, but I’ve heard the red, yellow, green method works, so can we go with that?”

Jester raised their eyebrows at the no safe words thing but said nothing else. “Okay. I usually use that anyways. Is there anything you really like?”

“I do like domming, but I am more used to being submissive. Same with topping; I enjoy it, but I am used to being the bottom. I just need a little extra lube because testosterone means I do not make it as much as I used to?”

“Alright. You in the mood to sub for me?” Their voice was low and dangerous and holy shit, was it a turn-on.

“Please,” Caleb moaned.

Jester’s grin was glorious. “Okay. Let me take you to my room, then.” She took his hand and led him down the hallway to the bedroom. It was a little plain, with one side decorated and the other side bare, but still having some tape residue and torn off corners of old posters. Jester pulled Caleb in by the lapels, smiling as she said, “Why don’t you undress?”

“Yes, uh…” Caleb paused as he fussed with the first button. “What should I call you?”

“My name is fine. So is mistress. Master I’m okay with, but it’s not my favorite.”

“Can I call you like...Mx. Last-Name?” Caleb asked.

“Mx. Lavorre works just fine.” Jester smiled a little, clearly pleased that he thought of a way to keep things neutral.

“Okay, Mx. Lavorre,” said Caleb with a smile as he undressed. He wasn’t ripped by any means -- if anything, he was rather skinny -- but when he took off his shirt, Jester’s whole body shifted. Her eyes went up and down his chest, and one hand moved to his top surgery scars.

“You’re gorgeous, Caleb,” Jester muttered.

“Thank you, Mx. Lavorre, but you outshine me in all regards.” Caleb leaned in to kiss Jester again. She reciprocated, but pulled away briefly.

“Just because I’m beautiful doesn’t mean you’re not. I don’t want you to self-deprecate yourself, okay? I won’t punish you for it, but I will point it out and correct it. Okay?”

Caleb took a deep breath. Astrid had never done that for him. This was definitely new. But he nodded and said, “Yes, Mx. Lavorre.”

Jester’s smile returned as she kissed him with vigor, leading him to the bed, pushing him down onto it. She was impressively strong for her size. Holy shit, that was hot. Then they stopped and paused to think. “Hm...should I torture you by undressing now, or should I have you undress?”

“I do not mind either way,” said Caleb with a shrug.

They looked him up and down and asked, “Do you like begging for things?”

“As long as you don’t take it too far, I am fine with it,” replied Caleb. “And again, do not mock me.”

“Okay...how would you feel if I asked you to beg to take my clothes off?” She raised her eyebrows, running her hands up her thighs. She was wearing a bright pink sleeveless dress with a little ruffle around the top of her breasts. It looked pretty stunning with her tan skin.

“Uh…” He had to take a moment to think because he was currently blue-screening a bit. “Ja, ja. That would be nice, Mx. Lavorre.”

“Alright. I’d like you to begin.” She smiled, moving closer, reaching out to trace the inside of his thigh through his jeans.

Caleb took a deep breath, relaxing onto his back. He was the most responsive in bed when he was relaxed. The booze was helping, but he still wasn’t drunk drunk; his German genes made him a bit harder to get completely wasted. After a few moments to get in his headspace, he begged in a deep, low voice, “Oh, Mx. Lavorre, please, I want to see you.”

“Good. More, my dear.” Jester was smiling proudly, clearly very amused. Their glancing touches moved closer and closer to between his legs. He gripped the sheets, wanting and wanting but trying so hard to be good.

“Please, Mx. Lavorre, I want nothing more to see you. I am sure you look gorgeous without anything on. I just want to see you. Please.” His voice was becoming more strained as he was getting more wound up. He just wanted to be touched, to see her undress, anything.

Jester pressed a hand against his cock and cunt, hard, eliciting a moan from him. She leaned down over him and whispered in his ear, in a harsh whisper, “Tell me exactly what you want me to do to you, Caleb.”

“I want you to undress,” he said, voice slowly becoming bolder, eyes locking with hers, “and I want you to fuck me.”

“You’re forgetting something, Caleb,” Jester said, going lighter on his dick.

Caleb was normally an obedient sub, but maybe it was something about Jester, or, you know, all the whiskey he’d had, but something made him want to break from the norm. Just a little. He smiled a bit cockily and repeated, “I want you to undress and I want you to fuck me, Jester.”

Jester pulled away, sighing. “I didn’t peg you as a brat, Caleb, but I guess you’ve shown yourself to be one. You were so clever to come up with that name for me. I thought you’d be good enough to use it.” She shrugged. “Oh well. Guess I’ll have to just tease the hell out of you.”

“I mean...I will not complain--”

“Shush. Naughty boys don’t talk unless they’re told to. Got it?”

Caleb nodded, blushing a little, but not feeling too bad with the chiding. “Yes, Mx. Lavorre.”

“Good. And no touching! Sit up, hands by your sides and on the bed at all times. Okay?”

“Yes, Mx. Lavorre,” said Caleb. He sat up and placed his hands exactly where she instructed them to bed. For the first time in a long while, he noticed he wasn’t slouching.

“There we go. Getting better, Caleb.” Jester moved their chair over from their desk, a really nice office chair on wheels, and dug through the bottom drawer of their dresser. “Hm…” they said, a bit theatrically, “do I wanna fuck myself or do I wanna play with my clit?” They grabbed two toys, one a big wand with a nice rubber head, the other a long dildo, with a huge bottle of lube as well. “I think I want both,” they said with a cheeky smile. Jester turned to the chair and sat down. They took off their panties, these patterned boyshorts with lace trim, and tossed them aside, quickly closing their legs so Caleb couldn’t see what lay between them. They turned the chair to the side while they turned on the vibe and inserted two fingers in themselves. Immediately, their reaction was clear. Either they were really showing off, or Jester moaned like mad as a default. Gods, their laugh and smile went straight to his chest, but their moans went straight to his cunt, and he wanted nothing more than to ride them like his life fucking depended on it.

But if he wanted to do that, he knew he had to earn it.

Which meant watching Jester use her fingers and the vibrator to get one orgasm, then a second. Which meant watching her grab the dildo and slathering it with lube before rubbing it against herself, before sliding it in her, before giving Caleb a profile view of her taking nearly the whole damn cock like it was nothing.

Holy shit.

Another orgasm went through her. He could almost  _ hear  _ her squirt. Then another, less dramatic than the last. She finally turned off the vibe and set the dildo and wand aside on her desk. “I’ll clean that up tomorrow.” She grabbed the lube though, and brought it to the bedside table, setting it down with a slight thud. The sound made Caleb shiver a bit. Then Jester turned and sashayed over, coming very close to Caleb. She looked him in the eyes and asked, “Did you like my little show?” as one hand went to pet his hair and the other cupped his cheek. It was...remarkably tender. He had not expected it.

“Uh, ja. Yes, Mx. Lavorre.” He looked at her with a soft smile. “It was very lovely.”

Jester nodded. “I just wanted you to know that I don’t really think you’re bad or anything. This is just all for fun, okay?”

“Oh, ja, I know. I am aware.” Caleb almost wondered why she would assume that.

“Okay. I just...I’ve had some bad experiences with Rob, and I don’t want to repeat that experience with any of my subs, okay?” She looked him deeply in the eyes and there was this...care he had not expected. It made him exhilarated and calm all at once.

“Alright. Thank you.” He smiled at her more. Then they leaned in and kissed his forehead and…

Oh god.

Oh no.

This was all too soon, too fast. He couldn’t be feeling feelings  _ now _ , of all times, with someone he was probably going to leave in the morning and never see again, especially when he was just dumped by someone. No. This was a Jenga tower of bad decisions, and sooner or later the blocks would fall.

But he was sad and lonely and so,  _ so  _ desperate for affection.

So he went with it. He asked, “May I touch you?”

She nodded. “Of course. You’ve been good.”

His hands slowly drifted up to their hips, their waist, touching them over their dress. They leaned down and kissed him, softly. It was sweet and gentle and perfect. A balm to the wounds of his past. He never wanted it to end. Eventually Caleb broke off the kiss and muttered, “Can we just do this for a while? Please?”

“Of course!” Jester said with a smile. “I’d love to.” They crawled onto the bed and pressed up against him, kissing him deeply. It was bliss. Their lips were soft and their breath was sweet and they kissed like a master. This was different from Astrid, who was force and tongue and took your breath away but never gave any back. Jester was more push and pull, letting the flow between them shift as they kissed. 

Caleb loved it way too much to be safe.

He indulged in it anyways.

Eventually things shifted, got more heated again. The kisses were all breath and their hands were wandering everywhere, anywhere. Jester shifted so that she was on top, straddling one of his legs as she ground down shamelessly, moaning into Caleb’s mouth. “Caleb,” they said, lips ghosting over his.

“Jester,” he replied.

They sat up and unzipped their dress, slipping it off and tossing it aside. Suddenly, they were in nothing but a bra, and holy shit, Caleb had not noticed how gorgeous their chest was, but before he could even get a proper look, they were unhooking it, throwing it off as they let out a breath of relief. They moved back towards them, and gods, were they gorgeous. Caleb’s breathing was harsh and stuttering. He was so fucking horny. Jester rubbed his cunt through his pants and he moaned as though they were touching bare skin. They smiled. “How bad do you want me, Caleb?”

“Gods, I want you so bad, Mx. Lavorre. Please.” He was squirming, desperate for touch, for relief. 

With a grin, Jester undid his belt and pants, sliding them off, before taking off his boxer briefs as well. “Fuck, you’re gorgeous,” she said, eyeing his cunt and dick hungrily. “Also, holy shit, you’re big.”

“Testosterone is a miracle,” Caleb joked. “A sign the gods love us.”

Jester laughed then said, “Real quick, though, have you been tested recently?”

Caleb sighed, frowning. “No. Never thought to. Astrid and I were fluid bonded.”

“Ah. You should probably do that, considering the whole thing with them. Until then, I’m not going to put my mouth there, okay? But I can use a toy or my fingers?”

“Sounds fair,” Caleb said. “Frankly, I’m pretty sure if you breathed on me, I’d cum.”

“True.” She laid down next to Caleb, grabbing the lube from the nightstand and putting it on her hands. She slicked her hands up, then moved the slipperiest one down to his cunt and rubbed.

Caleb had never moaned so loudly, so desperately in his life.

Her fingers were cold, but that was unimportant. He held onto her, wrapping his arms around her as he buried his head in the crook of her neck so he could moan sweet curses to her skin. “Fuck, gods, please, I need your fingers, I need something in me now, fuck, fuck.”

Jester smiled. They grinned and said, “Why don’t you put that mouth to good use and make some marks? I want everyone to know I got pleasure from someone tonight.”

“Ja, Mx. Lavorre. I can do that.” Caleb’s teeth weren’t sharp, not by any means, but he’d learned what kind of pressure made bruises. He moaned as they touched him more, pausing to whimper and squirm while Jester moved to his cock, almost jacking it off a little.

“Get back on task, Caleb,” Jester commanded, voice teasing but firm. He obeyed like a good little thing, returning to the soft skin of her neck as she began slowly inserting her fingers in. He wanted so desperately to moan and whimper and sigh; her touch was that of an expert, and he was already so close.

But he would be good. Good for them.

When Jester was satisfied with the amount of marks he’d made, they said, “Hey, Caleb.”

“Ja?” Caleb pulled back, laying flat on the bed.

“Can I leave some marks on you?”

Normally, Caleb would say no. Had it been Astrid, he would’ve said no, at least in the past few years. But Jester...he liked the idea of getting marked by her. He liked the idea that he was owned by someone else, someone who wasn’t a lying, cheating asshole who left him because he just so happened to be poorer than some other lying, cheating asshole. He liked the idea of being someone else’s, if only for a night.

“Please,” he said, and she went nuts. Her teeth were a bit sharper, and her nips a bit more reckless, but never enough to draw blood. Meanwhile, she was fucking him hard with her fingers, expertly rubbing his prostate as he moaned more. 

“Louder, Caleb,” said Jester quietly. “I want the whole damn apartment to know I’ve got a new man in my bed.”

Caleb was never loud in bed, but hearing that made him want to be. So he moaned louder until he was practically screaming, and then suddenly he was cumming, squirting all over Jester’s hand as he yelled. As soon as it was over, his body was limp and tired and his breath was quick and tight.

“That was perfect, Caleb,” Jester said, covering him in little kisses.

“Thank you, Jester,” he said, tiredly. She leaned in and kissed him. Their kisses were soft and messy but true. Caleb was liking this, loving this softness, these gentle moments.

“To check in, you all good?” Jester asked. They brushed some of his hair from his face with delicate fingers. 

He smiled softly. “Ja, definitely. More than good. It has...been a while since I have had sex. Much less good sex with someone who honestly gave a shit about me.”

Jester nodded, a bit sadly. She relaxed a bit, half laying on top of him. “Yeah, me too. I mean, like I’ve been masturbating and shit. Like the first thing I did once Rob was gone was masturbate, and I’ve been doing it regularly ever since because I have a crazy high sex drive. But like...looking back, I feel really stupid for not dumping him sooner. He never gave a shit about me. It was all about him. Even sex was just about him cumming, him getting off, him feeling good. Didn’t matter so much what I felt.”

“Was he...abusive?” Caleb’s eyebrows raised.

“I mean…” They sighed. “I don’t know. I’m not ready to address that question just yet. I haven’t had enough time to assess things.”

Caleb nodded. “Fair.”

“Was Astrid?”

After a moment’s consideration, Caleb shook his head. “No. She was not abusive. Just...distant. The whole breakup was sudden. I thought things were just...settling as we were growing up? And sure, I can see the problems now, but...no, it was never abusive. Not truly.”

“That makes sense. Things are just so messy for me because Rob was such a raging dick that I don’t know what was just normal assholery or him actually being abusive.”

“I am sorry.” Caleb kissed her forehead.

“Thank you.” Jester snuggled up to him. After a moment, she started snickering. “I’m sorry, I just...thought of a literally raging dick and...my brain went to _ penis barbarian _ ?”

“What?” Caleb laughed in confusion. “What led you to that conclusion?”

“Well, so, Rob has always had these phases where he’ll be super into this one hobby and he’ll spend his whole paycheck from his dad on stuff for it before abandoning it within, like, three months, tops. And around the last birthday I spent with him a few months ago, he was super into D&D. All he wanted was the books and money for minis and dice. I refused to buy him minis or dice because frankly, his taste is awful, but I bought him  _ all  _ of the books for fifth edition. I already had birthday money saved and shit, but I dug a little further into my commissions and gave him a huge ass collection. And he, being the lazy shit that he is, didn’t want to learn any of it, so he convinced me to be his DM for him and his friends. So I spent weeks reading everything, getting ready to do a campaign, and session one rolls around, and they’re a bunch of drunk assholes and creeps who break my campaign so I just TPK’d them and stormed out. He blamed me for ruining the night and dropped D&D shortly after that. I did make him leave the books here, so there’s that.”

“That sucks. All that preparation gone to waste.” Caleb sighed. “Gods, I haven’t played that game in forever.”

“I wish my friends were here, or like, not ridiculously busy. I wouldn’t mind playing again with people who I know won’t be huge dicks.”

“Ja. That would be fun.”

Silence settled between them. Caleb noticed that the silences between them were getting more comfortable. It was nice. Caleb liked it.

After a minute, Jester looked up at him. “You alright to go another round or should we call it quits here?”

Caleb was a little tired, but still wanted more. “I might need some time to warm up again, but I can try making you cum?”

“Alright. Again, I’m not comfortable with anything other than fingers or toys right now, not until you get tested. Sound good?”

“Of course.” Caleb rolled over and kissed them, smiling. His hand cupped her cheek, stroking it softly with his thumb. Things were slower now -- it was getting late, and they were both tired -- but there was still this underlying heat that Caleb adored. He’d missed this. Missed spending time in bed, kissing someone who cared. Eventually, his hand wandered towards her chest, kneading her breasts softly. She moaned ever so slightly, not the big ones she’d made when she was masturbating, but it was a tiny, cute noise he wanted to hear more. So his lips moved down to her neck as he continued playing with her chest. “May I make more marks?” he said, lips occasionally glancing against her skin.

They nodded. “Yes. Please do.”

“Thank you, Mx. Lavorre,” he said, keeping up the play despite their lessened intensity. He made more marks besides the pretty red ones that had formed already. Once he felt their neck was adequately covered, he asked, “Can I make more on other places?”

“Definitely. I intend on showing off your work anyways.” She giggled slightly as he trailed down to her collarbone. One hand wrapped around his shoulders, the other reached up to his short, messy red hair and combed through it. “Is it okay if I do that? Go out in public, share selfies with my friends? Talk about what a great fucking night I had?”

“Sure. I do not mind.” It wasn’t like he was likely to cross paths with her again anyways. New York City was big, and he didn’t live in this area anyways.

“Sweet. I want to post a billion selfies. I assume I shouldn’t tag you?”

He shrugged. “I do not really use social media anyways.”

“Fair.” She smiled and sighed. His teeth and hands started eliciting more moans from her. “I gotta say, so far? You’re  _ way  _ better than my ex.”

“And I have not even made you cum yet.” Caleb smirked a little.

“Trust me, you don’t even have to do that. He set a low bar.”

Caleb joked, “Maybe you should date me instead,” then immediately realized what he said and stopped. Okay, maybe he was drunk.

He did not know if it was better or worse that Jester giggled in response. “Maybe so.” He turned a bright red and tried to continue on with his task of making marks as his hand drifted lower. They smiled as he traced his fingers over their body. “I would totally date you if you wanted,” they continued, just kind of blurting it out. Caleb looked up at them. “Like, you’re really sweet and gentle and you don’t seem like a jerk or anything.”

With a sigh, Caleb said, “You shouldn’t trust people so easily. You’ve just been cheated on and dumped.” His fingers drew swirling patterns along her stomach.

“Well just because someone hurt me doesn’t mean I should never trust  _ anyone _ . Besides, you’ve been hurt in the same way.” She ran her fingers through his hair, face suddenly sad. “If anything, you were hurt worse. Ten years. That’s a lot of time to lose.”

“Ja,” he said, nodding. “It is nice, knowing someone who understands.”

“Yeah.” She leaned down and kissed his head. “We can talk about it more when we’re not as boozed up.”

“That sounds like a good idea.” He kissed her chest, not wanting to bruise them now, wanting to be soft and sweet. “And I still have yet to make you cum.”

“You do....” Jester giggled again before his hand drifted down to her clit, rubbing slowly. She sighed as he touched it. Then she smiled. “I like how you actually know how to touch a vagina.”

“I’m guessing Rob was clueless?”

“Oh my fucking god, the man didn’t have a fucking clue--” Her voice was cut off by a moan when Caleb began rubbing in earnest. She smiled. “Fuck, that feels good!”

“There is some advantage to having a vagina, I suppose,” he said, grinning.

“Does it ever bother you?” she asked.

Caleb shook his head. “Not really anymore. I’ve stopped having periods at this point, thank god. And I’ve learned to at least not hate myself. Not anymore.” He sighed. “Though those first years after realizing, and then coming out...they were messy, that’s for sure.”

“Yeah. I haven’t even come out to my friends about being nonbinary yet. I don’t really have dysphoria but...it’s annoying, sometimes, being presumed to be a woman just because you have tits and wear dresses and pink stuff.” They sighed. “I’m killing the mood, aren’t I?”   
  


“We both are,” Caleb admitted. He moved himself up to her lips, kissing her softly as he continued rubbing her clit. She moaned so prettily into his mouth, it was addictive. “You are so fucking gorgeous.”

“Thank you. You are too, Caleb.” Jester extended his name in a way he loved. Cay-leb. It sounded good. It sounded right. He smiled when they said it, kissing them again.

She pulled away to moan when he rubbed her just right. Her moans were almost like squeals at this point, and Caleb chuckled. “You are also adorable.”

“I know,” Jester giggled. “So are you.”

“Are you just going to turn every compliment I give you onto me?” Caleb asked.

“Maybe.” Jester kissed him again.

“Guess my hand on your clit is not distracting enough, then?” He grinned, lowering his fingers to their hole. 

“Mmmm...maybe,” she giggled. “Though feel free to do both. I usually like both.”

“Hm. Alright, let me see.” Caleb tried to insert his fingers into her and rub her clit with his thumb. “This good?”

Jester made a face. “It’s fine.”

“No, it clearly is not.” He sorely wished he had been tested now, since he could easily finger her while using his mouth on her clit. “Can you use your vibrator?”

“Possibly? I’d have to be careful or I could burn my clit.”

“True.” Caleb sat up and deliberated how he was going to do this.

“I could use my hand?”

Caleb nodded. “Ja, that could work.” He laid back down and rubbed her cunt as she rubbed her clit. Once he was satisfied with how wet she was (very), he slipped two fingers in. She wasn’t tight -- she had fucked a pretty damn thick dildo earlier that night, after all -- but her moans were so fucking beautiful. After a few minutes of using only two fingers, he slipped a third one in. A bit tighter, but not bad. She showed no discomfort, didn’t use a safeword. Once he got going, her head fall back and she began to pick up speed on her clit.

“I’m close,” she whimpered, toes curling as her free hand gripped the sheets. “I’m so fucking close, Caleb. Make me cum.”

He sped up his thrusts, curling his fingers in a bit more to hopefully hit their g-spot. It seemed to be working like a charm, because within seconds, they were cumming like a freight train, crying out loudly, body tightening as he felt the clench of their cunt on his fingers. Once the orgasm had passed, he pulled his fingers out of them, grinning widely. They were out of breath and sweaty, but their grin was encapsulating.

“Yep. Better than my ex.” She drew Caleb closer, pulling him on top of her. “That was really fucking good, Caleb.”

“Well, you helped,” Caleb said, hiding his face in the crook of their neck.

“Yeah, but you still beat out Rob. I keep telling you, this guy set a low bar.”

Caleb paused. “Did you date anyone before him?”

“No, not really. I kissed like, two other people before him? And those times never went anywhere. Then he swept me off my feet, la-dee-dah, only to pull the football away from me and leave me flat on my back.”

“Uh.”

“Peanuts reference. Charlie Brown? With Lucy and the football?”

“No idea what you’re talking about.” Caleb shook his head.

“What? You haven’t heard of that? Oof. I’m gonna have to break out the old DVDs when we do this again.”

“When?” he repeated, looking up at her to see if she was serious.

“I mean...do you not want to do this again?” She looked at him, concerned.

“Uh. I do. But...you would have sex with me again?”

“Caleb,” Jester cupped his cheeks, squishing them a little. “You are super hot, amazing in bed, and you’ve been nothing but sweet to me. You better believe I would bone you again.” She kissed him, smiling. “Speaking of boning...do you want to continue?”

Caleb grinned, feeling a blush coming on. “Ja, if you do not mind. I think one more round would be nice.”

Jester kissed him once more, then got up and dug around in her drawer again, fishing out a dildo with an upturned bulb instead of a flat base at the end and a strap-on harness. “I got this as soon as Rob left. If he saw me get this, he would be offended, I think.” She grabbed the lube, spurting a small amount onto her palm so she could slick up the bulb part.

“He’s lame,” said Caleb, chuckling. “At least Astrid and I had a fulfilling sex life at some point.”

“I mean, sex wasn’t bad at first. But then he turned out to be a big one trick pony.” Jester separated their legs a bit awkwardly, sticking the bulb into their cunt. Not terribly sexy in and of itself, but the anticipation was enough to make Caleb’s skin buzz and warm.

He tutted. “Damn. I hope that I can keep up with you, if we make this a regular thing.”

“You’re a vers and a switch. That’s already more than enough room to have fun with.” They smiled, grabbing a small towel from the first drawer of the nightstand to wipe off their hand, then taking the harness and putting it on. Once it was strapped up properly, they...looked really damn hot. Caleb’s breath slowly quickened as he propped himself up on his elbows. Jester grinned when they saw his excitement. “You wanna ride me, Caleb? Or should I be on top?”

“I’d like to ride you, if you don’t mind, Mx. Lavorre.”

Jester giggled. “Alright. You think you’re wet enough? I’m gonna add lube to this anyways, but do you need some yourself?”

“I think I’m fine?”

“How about warming up? You want to do that, too?” Jester took a condom and slid it on the cock, then added a tiny bit more lube to it.

“Nein, I should be alright.”

“Good!” Jester grinned as she wiped off her hand, getting on the bed, laying down on her back. Caleb shifted to make room for her and straddled her thighs, rubbing his cunt. 

“Fuck,” he said softly, realizing now how wet he was again. “Oh, ja, I should be fine.”

“I’ll keep it accessible just in case,” Jester said sweetly.

Caleb grinned. She...really cared. Astrid had never really been like that. “Danke,” he said softly, pausing to look at her warmly. Then he realized what he was doing and moved, lining up the dildo so he could slowly, slowly get it inside of himself. As it pushed in, Caleb moaned, eyes fluttering shut as he took her.

“That good?” Jester asked, patting Caleb’s thigh.

“Fuck, ja,” he said softly. Once he was fully on her, Caleb began to move his hips slowly, grinding a little. He moaned as he felt the dildo rub against his prostate. “Jester,” he said, forgetting his proper name for her. “Jester.”

They smiled, not seeming to mind. Their hands rubbed up and down his hips and thighs and stomach as they moaned softly. “You enjoying yourself, Caleb?” Jester asked, giggling.

Caleb nodded. “Oh, ja. Definitely.” He slowly, slowly picked up speed, moaning as he did so. He began to lose himself, muttering in German, “ _ Oh, fuck, Jester, Jester, please, darling, you feel so good, so wonderful, please. _ ”

Jester giggled. In German, with a low, commanding voice, she said, “ _ You sound so pretty, Caleb. Shall I take the lead? _ ”

On the one hand, being caught calling Jester “darling” was a bit embarrassing. But her  _ accent _ , her  _ voice _ , her  _ tone _ threw him off. He moaned and nodded. “Bitte,” was all he could say.

Jester smiled, keeping Caleb on her but slowly moving her hips, fucking up into him. She was  _ strong _ , able to hold him up and fuck him. Beneath the soft fat was tense muscle that made her all the more attractive.  _ Fuck _ , he was falling.

Before Caleb knew it, he was crying with an orgasm.

A few seconds later, he collapsed into her arms, panting and tired. She giggled, kissing his forehead. “That was really nice, Caleb,” she said, soft and giggly.

“Ja,” was all he could say.

They laughed. “Did I fuck your brains out?”

“Maybe.”

Jester moved him to the side so they could pull out of him, making him groan one last time. “I’m gonna clean up a little. You mind sleeping here, or should I dress you and take you home?”

“Sleep here,” he said.

“Alright.” Jester pulled the blankets up from under him and tucked him in tight, kissing him on the forehead. “You get some sleeping, Caleb, okay?”

All Caleb could do was nod as he felt Jester taking off his glasses. It only took him a moment to fall asleep.


End file.
